A Luxury Rental 30 - Vacation Rentals in Windham Mountain Resort

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From US $231

         

9.0 (54 Reviews)

House

TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores

• Air Conditioner
• Parking
• TV

• Kingston
• Windham

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From US $730

         

|

10.0 (4 Reviews)

House

Catskills Mountain Retreat - Luxury Meets Serenity

• Air Conditioner
• Parking
• Pet Friendly

• New York
• Jewett

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From US $146

         

|

9.0 (125 Reviews)

Bed & Breakfast

Antique Rose Inn Windham

• Air Conditioner
• Parking
• TV

• Kingston
• Windham

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From US $388

         

10.0 (40 Reviews)

House

Red Fox Townhouse & Alpine hot tub 1 minute to ski slope, bars & ski town

• Air Conditioner
• Parking
• TV

• Kingston
• Windham

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From US $324

         

|

10.0 (3 Reviews)

House

4 Mi to Windham Mountain Ski Getaway!

• Parking
• Accessibility
• Security/Safety

• Kingston
• Hensonville

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From US $247

         

|

9.0 (28 Reviews)

Bed & Breakfast

Georgian Garden Inn

• Parking
• TV
• View

• Kingston
• Windham

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From US $474

         

10.0 (35 Reviews)

House

'The Mountain House:' Windham Retreat w/Hot Tub!

• Air Conditioner
• Parking
• TV

• Kingston
• Windham

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From US $675

         

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10.0 (2 Reviews)

Ski Chalet

Fantastic 2 family vacation home with EV charger

• Parking
• Balcony/Terrace
• Security/Safety

• Kingston
• Windham

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From US $222

         

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7.4 (68 Reviews)

House

Beds on Clouds

• Air Conditioner
• Parking
• TV

• Kingston
• Windham

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From US $279

         

9.8 (50 Reviews)

House

2 Bedroom Townhouse in front of Windham Mountain Ski Resort

• Air Conditioner
• Parking
• Pool

• Kingston
• Windham

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From US $553

         

8.8 (18 Reviews)

House

Slope Views: Luxe Windham Retreat w/Hot Tub!

• Air Conditioner
• Parking
• TV

• Kingston
• Windham

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From US $521

         

10.0 (69 Reviews)

House

Mountain house with Scandinavian BBQ hut and Hot tub

• Air Conditioner
• Parking
• Pet Friendly

• New York
• Jewett

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From US $234

         

10.0 (69 Reviews)

Cabin

Cutest Cabin in Windham epic location

• Air Conditioner
• Parking
• TV

• Kingston
• Windham

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From US $323

         

10.0 (66 Reviews)

House

Custom Built Luxury Cabin on 2.5 Acres, 10 Mins to Windham & Hunter Mountains!

• Air Conditioner
• Parking
• TV

• New York
• Jewett

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From US $497

         

10.0 (61 Reviews)

House

Timber frame home only 5 minutes from Windham Mountain - perfect for 2 families!

• Air Conditioner
• Parking
• Pet Friendly

• Kingston
• Windham

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From US $783

         

10.0 (52 Reviews)

House

Luxury Log Cabin-Windham Mountain. Amazing sunsets, large lawn, deck, fireplace

• Air Conditioner
• Parking
• TV

• Kingston
• Windham

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From US $810

         

10.0 (26 Reviews)

House

River & Golf Mountain Retreat

• Air Conditioner
• Parking
• Pet Friendly

• Kingston
• Windham

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From US $659

         

10.0 (25 Reviews)

Cabin

Woodpecker House - One of Vrbo’s 2025 Vacation Rental of the Year

• Air Conditioner
• Parking
• Pet Friendly

• New York
• Jewett

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From US $657

         

10.0 (25 Reviews)

House

"New Home" Idyllic Mt Views ,Pond & Horse farm views 2 min to Town

• Air Conditioner
• Parking
• TV

• Kingston
• Windham

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From US $1,242

         

10.0 (23 Reviews)

Condo

5-Star. Luxury Condo, Heated Pool, Hot Tub, Ski in/out @ Windham

• Air Conditioner
• Parking
• Pool

• Kingston
• Windham

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From US $620

         

10.0 (19 Reviews)

House

Luxury Home w/Deck: Explore the Catskill Mtns!

• Air Conditioner
• Parking
• TV

• Kingston
• Windham

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From US $510

         

10.0 (16 Reviews)

House

WINDHAM HOME SLEEPS 10 - 1 MILE TO SLOPES !

• Parking
• Pet Friendly
• TV

• Kingston
• Hensonville

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From US $794

         

10.0 (14 Reviews)

Condo

Condo in Windham Mountain Village

• Air Conditioner
• Parking
• Pet Friendly

• Kingston
• Windham

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From US $525

         

10.0 (13 Reviews)

House

Located within 10 minutes from both Windham Mountain and Hunter Mountain!

• Air Conditioner
• Parking
• TV

• Kingston
• Hunter

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